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Private wooded lot- Updated Baileys Harbor Home

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Welcome to The Roost!
Enjoy a bonfire during your get-a-way!
Wood burning fireplace
Great open layout
Room for everyone to gather and unwind

Reviews

9.8 out of 10
Exceptional
3 bedrooms2 bathroomsSleeps 6154.1 sq m

Popular amenities

  • Washing machine
  • Dryer
  • Pet-friendly
  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

1 Single Bed and 1 Queen Bed

Bedroom 3

1 Queen Bed

Common Area

1 Double Sofa Bed

2 bathrooms

Bathroom 1

Bathroom 2

Spaces

Deck or patio
Garden
Dining area

About this property

Private wooded lot- Updated Baileys Harbor Home

Welcome to The Roost, hosted by Simple Life Rentals! Updated in 2023, this 3 bedroom, 2 bathroom, 1-story home showcases beauty in all the details. The home is situated on a private road, nestled on a 2.25 acre wooded lot with a large pull through driveway perfect if you are towing a boat. Enjoy the peace and serenity of the woods with the convenience of a short walk or drive to downtown Baileys Harbor and Lake Michigan. Visit shops, restaurants, the harbor, The Ridges Sanctuary, and more!

This property allows up to 2 well-behaved dogs. There is an additional fee collected at booking.

Property Features:
+ Back patio with picnic table
+ Firepit with 6 chairs (please bring local firewood)
+ Yard games provided: tether ball, ladder golf, giant Jenga
+ Dog friendly - up to 2 dogs allowed
+ Internet Wi-Fi: Starlink great for working remote (due to the rural nature of the property, cell phone coverage can vary) 
+ Smart TV
+ Blu-Ray player and video library
+ Sound system
+ Central air and heat
+ Wood burning fireplace (bring local firewood)
+ Dining table with seating for 6. Snack bar offers seating for 4
+ Washer, dryer, iron, ironing board and drying rack
+ Board games, puzzles, books and toys provided for guest's entertainment
+ Wine refrigerator
+ Bench and mudroom like area in garage for shoes/ etc
+ Coffee bar includes a traditional drip coffee maker, a Keurig, a French Press, frother, coffee syrup flavors and a coffee bean grinder
+ Fully equipped kitchen (see amenities) includes ice maker, crockpot, and an additional full size fridge in the garage

Sleeping Accommodations:
Bedroom 1: King size bed, ceiling fan, room darkening shades, hangers, extra pillows and blankets.
Bedroom 2: Bunk bed set offers a twin size bed over a queen size bed, room darkening shades, ceiling fan, hangers, extra pillows and blankets.
Bedroom 3: Queen size bed, ceiling fan, room darkening shades, hangers, extra pillows and blankets.
Additional sleeping space: Pull-out sofa couch in living room  (full size bed)

Bathrooms:
Bathroom 1: Full bathroom w/ a soaking tub, walk-in shower, double vanity, and hair dryer.
Bathroom 2: Full bathroom w/ tub and shower combo and hair dryer.

Our property is conveniently located the following distances from nearby favorites:
3 miles from Kangaroo Lake and the Causeway
12 miles from Cave Point County Park and White Dunes State Park
8 miles from Fish Creek, 8.5 miles from Ephraim, 9.6 miles from Sister Bay, 10 miles from Egg Harbor, 15 miles from Ellison Bay, 20 miles from Gills Rock

Amenity + damage protection waiver includes:
• Bed linens, pillows, blankets, and bathroom towels. (Please bring your own beach towels)
• A starter pack of essentials which includes toilet paper, paper towel, dish soap, dishwasher soap, hand soap, and garbage bags. Due to septic systems, we do not provide facial tissue. One each of travel size shampoo, conditioner, and body wash per full bathroom.
• PEACE OF MIND Damage protection covers up to $1000 per stay for accidental damage that is reported prior to departure (excludes any pet damage).

Home Truths:
This is a quiet community with residential neighbors. This home is geared towards quiet family vacations. Due to the proximity of neighbors, we cannot accommodate bachelor or bachelorette parties, reunions, or other rowdy gatherings.

Door County Tourism Zone Commission Permit #02-56-2886-07

Please be aware that you must sign a terms and conditions agreement, which will be sent to you separately, to finalize your reservation.

Add dates for prices

Amenities

Washing machine
Dryer
Pet-friendly
Free WiFi
Air conditioning
Outdoor space

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Baileys Harbor

Located in Baileys Harbor, this holiday home is in a rural area. The area's natural beauty can be seen at Lake Michigan and Peninsula State Park, while Door Shakespeare and Birch Creek Music Performance Center are cultural highlights. Peg Egan Performing Arts Center and Pirate's Cove Adventure Golf are also worth visiting. Take in the nearby slopes with cross-country skiing, or try out other outdoor activities such as ice skating.
View more Holiday homes in Baileys HarborOpens in a new window
Map
Baileys Harbor, WI

What's nearby

  • Door County Brewing Company - 16 min walk - 1.4 km
  • Anclam Beach Park - 20 min walk - 1.7 km
  • Baileys Harbor Ridges Park - 2 min drive - 1.8 km
  • Ridges Sanctuary - 3 min drive - 2.2 km
  • Cana Island Lighthouse - 14 min drive - 11.6 km

Restaurants

  • ‪Coyote Roadhouse - ‬7 min drive
  • ‪Sway Brewing + Blending - ‬10 min walk
  • ‪Door County Brewing Company - ‬16 min walk
  • ‪Koepsel's Farm Market - ‬9 min drive
  • ‪AC Tap - ‬8 min drive

Frequently asked questions

Is Private wooded lot- Updated Baileys Harbor Home pet-friendly?

Yes, pets are allowed at this property.

How much does it cost to stay at Private wooded lot- Updated Baileys Harbor Home?

As of 4 Apr 2026, prices found for a 1-night stay for 2 adults at Private wooded lot- Updated Baileys Harbor Home on 9 June 2026 start from AU$443, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Private wooded lot- Updated Baileys Harbor Home?

On-site parking is available at the property.

What time is check-in at Private wooded lot- Updated Baileys Harbor Home?

Check-in begins at 4:00 PM.

What time is check-out at Private wooded lot- Updated Baileys Harbor Home?

Checkout is at 10:00 AM.

Where is Private wooded lot- Updated Baileys Harbor Home located?

Situated in a rural location, this holiday home is within a 15-minute walk of Door County Brewing Company and Lake Michigan. Baileys Harbor Ridges Park and Anclam Beach Park are also within 2 miles (3 km).

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 18 out of 20 reviews
Rating 8 - Good. 2 out of 20 reviews
Rating 6 - Okay. 0 out of 20 reviews
Rating 4 - Poor. 0 out of 20 reviews
Rating 2 - Terrible. 0 out of 20 reviews

10/10

Cleanliness

9.8/10

Check-in

9.8/10

Communication

9.8/10

Location

9.6/10

Listing accuracy

Reviews

Verified

10/10 Excellent

TIna S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We appreciated being able to bring our dog, that was key to us.
Stayed 2 nights in Oct 2025
Verified

10/10 Excellent

Sandra V.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect Birthday stay in Door County. Lovely house decorated for holidays and VERY comfortable beds. Plenty of space for all and our pup to enjoy. Quite wooded area, very cool to see wild turkeys roost every night. Guessing that's why the house is called the Roost. Very easy in and out and to have a garage space to load and unload Fantastic!! Will reserve again soon :)
Stayed 4 nights in Dec 2025
Verified

10/10 Excellent

Matthew K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The property was very clean. In a wooded area that was nice & quiet. We were able to bring our dog which was a bonus. Plenty of places to walk her right out the door of the home. Arguably the most comfortable bed I've ever had at a rental property whether it be at a hotel or a home/cabin rental.
Stayed 3 nights in Oct 2025
Verified

10/10 Excellent

Debra C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Can't say enough good things about our experience at this home. The communication with the managing company was the most efficient and friendly I've ever had. The house was very clean and so comfortable with many amenities. We loved the wooded area and the fire pit was a bonus. We will definitely book again!
Stayed 4 nights in Sep 2025
Verified

10/10 Excellent

William v.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was not much to look at from the outside but the inside was beautiful. It was clean, modern and was stocked with anything you could want. Setting was very private and quiet, yet close to restaurants, and parks.
Stayed 4 nights in Sep 2025
Verified

10/10 Excellent

Virginia M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Clean and convenient

Nice place close to any where you may want to visit in Door County
Stayed 2 nights in Sep 2024
Verified

10/10 Excellent

Jodi J.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Very nice

Very nice place to stay and a quiet neighborhood
Stayed 2 nights in Jul 2023
Verified

10/10 Excellent

Mary D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Family Getaway

We really enjoyed our stay at The Roost. It was clean, cozy, comfortable and well appointed for our family. The location was also nice for the activities we had planned. Plus, it is pet friendly. I would stay at the Roost again and would higly recoomend.
Stayed 2 nights in Aug 2024
Verified

10/10 Excellent

Alex W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Good stay

Fun time! Good property and location!
Stayed 3 nights in Aug 2023
Verified

10/10 Excellent

Patricia P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wow! Location and amenities!

Convenient to everything in Door County, yet in a quiet woodsy setting. The home was fully equipped with what we needed for a long weekend with our adult children, their spouses and their sweet doggos. Relaxing and fun! Would rent this again in a heartbeat.
Stayed 3 nights in May 2025
Verified

10/10 Excellent

gwen l.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Door County getaway

The home was beautiful. I was impressed with how well furnished it was. Anything you wanted/needed was available. Very well decorated and comfortable. Quiet setting.
Stayed 4 nights in Oct 2024
Verified

10/10 Excellent

Michelle D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful home in a peaceful location

We loved our stay here! It was a quick drive to the places we wanted to visit, the neighborhood was very quiet, the home was beautifully uodated and all the amenities were thought of so we could relax and enjoy. The fire pit was a great place to visit and watching all the deer in the woods really made us feel like we were away from the hustle and bustle of town. We would love to stay here again next time we are in Door County.
Stayed 3 nights in Sep 2023
Verified

10/10 Excellent

MaryJane Steinthal K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay

We are a family with adult children and their spouses. We loved staying at the Roost. It felt more like home than a rental. It had all the amenities we could have wanted. Beds were comfortable, it was clean, and it a good location. We will be back!
Stayed 5 nights in Jul 2023
Verified

10/10 Excellent

Terri S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nicely Furnished Comfortable House

The house was very clean and nicely furnished. The owners put some thought into the decor. This house is within walking distance to Bailey’s Harbor, and in a quiet location. It’s also close to Maxwelton Braes and the Orchards Golf courses. Very easy to get to Egg Harbor and Sister Bay from this location.
Stayed 7 nights in Jun 2023
Verified

10/10 Excellent

Kevin A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay!

We had a great stay in Bailey’s Harbor. This property is very comfortable and very clean. Beautiful and private setting in a very wooded area but close to town and the lake. The house is completely updated with so many nice extras like a coffee bar, fireplace and cozy fire pit with plenty of chairs The decor is beautiful… comfortable beds and very nice linens and towels. I wish our stay was longer so we could have enjoyed the fireplace inside! No issues except we had trouble opening the lock box at first but then got the hang of it.
Stayed 2 nights in Sep 2023
Verified

10/10 Excellent

Jenna S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Cute with all the amenities

This house was so cute! It had a full modern bar cart, coffee and tea bar, s’mores tray with skewers, and a well-stocked kitchen. The fire pit was well-stocked with wood. The location was just far enough from the main drag that you couldn’t tell it was peak tourist season! We couldn’t find a big grocery store in Baileys Harbor, so did end up going to Sister Bay, which was only 10-15 minutes from the house. Overall we had a great time!
Stayed 2 nights in Jul 2023
Verified

10/10 Excellent

Melinda H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is a beautiful home; laid out well and very comfortable with a well equipped kitchen, which we only used for breakfast, but we appreciated it just the same. The only thing it didn’t have was a generator, which would have been nice when we lost power due to a very big storm; but we were grateful for a neighbor, Lurana, who came to check the house the next morning and supplied a couple of gallons of water so we could take care of essentials. We were also pleasantly surprised to receive a generous gift card to Chives from the owners to compensate for the inconvenience of the power outage. We were able to enjoy the use of that before we left DC and the restaurant was wonderful. Thank you for thinking of us in this way! We appreciated it very much.
Stayed 4 nights in Aug 2025
Verified

8/10 Good

Lisa H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic decor!

We weren’t sure if our boat was going to make it up the long wooded road and there was a car in the driveway when we got there so we were a little worried. It was the cleaning crew who had us come back half an hour later. When we got in there we were absolutely blown away!! The decor was top notch and the layout was awesome! All 3 of us loved this cozy home in the woods so much that we didn’t want to leave. This was our first air b&b stay and it was absolutely perfect!! There was so much thought put into everything in this home. We are so glad we chose this place for our anniversary getaway.
Stayed 3 nights in Jun 2024
Verified

8/10 Good

Charles X.

Liked: Cleanliness, check-in, communication, location
Stayed 2 nights in Oct 2025
Verified

10/10 Excellent

Becky B.

Stayed 4 nights in Jun 2025

About the host

Hosted by The Simple Life Hospitality

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Languages:

English

Premier Host

They consistently provide great experiences for their guests
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